Angewandte Chemie International Edition,
Год журнала:
2022,
Номер
61(24)
Опубликована: Март 25, 2022
A
palladium-catalyzed
chemoselective
coupling
of
readily
available
bicyclo[1.1.1]pentanyl
alcohols
(BCP-OH)
with
various
halides
is
reported,
which
offers
expedient
approaches
to
a
wide
range
cyclobutanone
and
β,γ-enone
skeletons
via
single
or
double
C-C
activation.
The
chemistry
shows
broad
substrate
scope
in
terms
both
the
BCP-OH
including
series
natural
product
derivatives.
Moreover,
dependency
reaction
chemodivergence
on
base
additive
has
been
investigated
through
experimental
density
functional
theory
(DFT)
studies,
expected
significantly
enrich
modes
increase
synthetic
potential
preparing
more
complex
molecules.
European Journal of Organic Chemistry,
Год журнала:
2024,
Номер
27(9)
Опубликована: Фев. 8, 2024
Abstract
Cycloalkanols
ring‐opening
transformation
is
one
of
the
most
valuable
and
wide
area
research.
Among
numerous
methods
that
have
been
developed,
transition‐metal‐free
approaches
attracted
great
interest
from
both
chemists
pharmacologists.
This
largely
due
to
advantages
being
environmentally
benign,
cost‐effective
operationally
simple.
Here
we
provide
a
comprehensive
outline
on
recent
advances
in
synthesis
distally
substituted
ketones
cyclic
compounds
via
cycloalkanols
under
conditions.
Advanced Synthesis & Catalysis,
Год журнала:
2024,
Номер
366(11), С. 2623 - 2628
Опубликована: Апрель 20, 2024
Abstract
A
palladium
catalyst
system
based
on
PdCl
2
(PPh
3
)
or
(dppf)
is
reported
for
Suzuki‐type
coupling
of
both
N
‐aryl
and
alkyl
benzotriazinones
with
aryl/alkenyl
boronic
acids
to
afford
a
series
ortho
‐aryl/alkenyl
benzamides
in
yields
up
99%,
showing
improvements
catalytic
efficiency,
substrate
scope
practicality.
Scope
limitations
the
improved
protocol
have
been
demonstrated
more
than
40
examples,
including
multigram‐scale
synthesis
activated
o
‐biphenyl
amide.
Large
electronic
steric
effects
from
acid
counterpart
observed,
implying
transmetallation
boron
should
be
involved
rate‐determining
step
cycle.
Organic Letters,
Год журнала:
2020,
Номер
23(3), С. 734 - 738
Опубликована: Дек. 15, 2020
Using
a
facile
and
cost-effective
method,
nine
bicyclic
1,2,3-triazine
2-oxides
were
synthesized
from
o-aminocyanide
substrates
through
an
unusual
nitration
cyclization.
The
reaction
mechanism
was
studied
experimentally
theoretically.
Moreover,
3-oxides
also
obtained
in
good
yields.
Chemical Communications,
Год журнала:
2021,
Номер
57(12), С. 1506 - 1509
Опубликована: Янв. 1, 2021
Silver-catalyzed
direct
C–H
functionalization
of
cyclic
aldimines
with
cyclopropanols
and
cyclobutanols
via
a
radical-mediated
C–C
bond
cleavage
strategy
has
been
realized,
generating
the
desired
products
in
decent
yields
wide
substrate
scope.
Organic Letters,
Год журнала:
2022,
Номер
24(31), С. 5741 - 5745
Опубликована: Авг. 2, 2022
A
nickel-catalyzed
denitrogenative
cross-electrophile-coupling
of
benzotriazinones
with
unactivated
alkyl
halides
(X
=
Cl,
Br,
I)
in
the
presence
manganese
powder
as
a
reductant
has
been
developed.
The
reaction
furnishes
ortho-alkylated
secondary
benzamides
modest
to
good
yields
under
mild
conditions.
scope
is
demonstrated
25
examples,
showing
tolerance
steric
hindrance
and
common
functional
groups,
thus
providing
an
efficient
protocol
benzamide
derivatives
without
use
preprepared
organometallic
reagents.
The Journal of Organic Chemistry,
Год журнала:
2022,
Номер
87(13), С. 8752 - 8756
Опубликована: Июнь 14, 2022
An
efficient
trifluoroacetic
acid-mediated
denitrogenative
hydroxylation
of
1,2,3-benzotriazin-4(3H)-ones
is
described.
This
metal-free
approach
compatible
with
a
wide
range
1,2,3-benzotriazin-4(3H)-ones,
affording
ortho-hydroxylated
benzamides
in
good
to
high
yields
short
reaction
time.
The
believed
proceed
via
benzene
diazonium
intermediate.
synthetic
utility
the
was
successfully
demonstrated
by
preparation
an
antimicrobial
drug,
Riparin
C,
and
benzoxazine-2,4(3H)-diones
yields.
Organic Letters,
Год журнала:
2022,
Номер
24(49), С. 9012 - 9016
Опубликована: Дек. 5, 2022
An
expedient
synthesis
of
benzo[c][1,2]dithiol-3-ones
via
metal-free
denitrogenative
transannulation
benzotriazinones
is
developed,
which
represents
the
first
example
acid-mediated
heteroannulation
benzotriazinones.
This
newly
discovered
reactivity
enables
streamline
diverse
in
decent
yields
by
using
sodium
sulfide
as
sulfur
source
under
simple
reaction
conditions.
Abstract
Cyclopropanols,
due
to
their
particular
chemistry,
can
participate
in
various
synthetic
reactions
with
retention
or
cleavage
of
the
strained
three‐membered
ring.
Direct
cross‐coupling
ring‐opening
reaction
such
molecules
access
organic
compounds,
as
ketones
has
great
importance
medicinal
chemistry
and
material
sciences.
Hence,
coupling
reaction/cyclization
cyclopropanols
for
constructing
new
valuable
presence
a
transition
metal
catalyst
under
metal‐free
conditions
is
described
this
context.
The
features
are
discussed,
mechanisms
challenging
highlighted.
